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Process for producing glycolide and glycolic acid oligomer for production of glycolide

a technology of glycolic acid and oligomer, which is applied in the field of process for producing glycolide and glycolic acid oligomer for production of glycolide, can solve problems such as adverse effects, and achieve the effect of lowering the reaction velocity and viscosity of the system

Active Publication Date: 2010-10-12
KUREHA KAGAKU KOGYO KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0023]The present invention adopts a solution depolymerization mode for depolymerization of glycolic acid oligomer effected in a solution phase containing an organic solvent from the viewpoints of suppressing the conversion of the glycolic acid oligomer into heavier products and efficiency of glycolide formation.
[0049]Examples of the compound (C) having an alcoholic hydroxyl group may include: monohydric and polyhydric alcohols (inclusive of partially esterified products and partially etherified products) and phenols. Alcohols are most effective as the compound (C) having an alcoholic hydroxyl group, and particularly a polyhydric alcohol having two or more hydroxyl groups in its molecule is preferred. Such a polyhydric alcohol has an advantage of a high boiling point even a low molecular weight so that it is not readily distilled out of the reaction system, and even a smaller amount of addition thereof can exhibit an excellent effect compared with a monohydric alcohol. The compound (C) may preferably have a boiling point of at least 190° C., more preferably at least 195° C.

Problems solved by technology

More specifically, it has been confirmed that nitrogen-containing substances in an amount calculated as ammonia have an retarding effect to depolymerization of glycolic acid oligomer as ca. 100 times as much as the impurity carboxylic acids in an amount calculated as diglycolic acid and also exhibit an adverse effect due to viscosity increase of the liquid in the reaction system.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Synthesis of Glycolic Acid Oligomer (a)

[0095]Into a 500 ml-glass-made vessel, 800 g of the above-obtained high-purity glycolic acid aqueous solution was charged and heated up to 200° C. under stirring at normal pressure to proceed with condensation while distilling out resultant water. Then, the pressure in the vessel was lowered to 5.0 kPa and held at 200° C. for 2 hours to distill off low-boiling point fractions including non-reacted glycolic acid, thereby preparing 400 g of glycolic acid oligomer (a) containing impurity carboxylic acids (A) at a concentration calculated as diglycolic acid (x) of 0.16 wt. % and nitrogen-containing substances (B) at a concentration calculated as ammonia (y) of 0.0002 wt. % giving an effective concentration (x+100y) of depolymerization-obstructing substances of 0.18 wt. %.

synthesis example 2

Synthesis of Glycolic Acid Oligomer (b)

[0096]A solution was prepared by adding glycoloamide (made by Aldrich Co.) so as to provide a concentration of 0.1 wt. % to the above-prepared high-purity glycolic acid aqueous solution. The procedure of Synthesis Example 1 was repeated except for using the solution instead of the high-purity glycolic acid aqueous solution per se to obtain glycolic acid oligomer (b). The nitrogen content in glycoloamide is 19 wt. % so that 0.1 wt. % of glycoloamide correspond to 0.02 wt. % of ammonia on an equi-molar basis, and it was multiplied by a condensation ratio of 2(=800 g / 400 g) to provide a nitrogen content calculated as ammonia in the oligomer (b) of 0.04%. Thus, the glycolic acid oligomer (b) contained impurity carboxylic acids (A) at a concentration calculated as diglycolic acid (x) of 0.16 wt. % and nitrogen-containing substances (B) at a concentration calculated as ammonia (y) of 0.04 wt. % giving an effective concentration (x+100y) of depolymeri...

synthesis example 3

Synthesis of Glycolic Acid Oligomer (c)

[0097]The procedure of Synthesis Example 1 was repeated except for using the above-mentioned commercially available glycolic acid aqueous solution instead of the high-purity glycolic acid aqueous solution to obtain glycolic acid oligomer (c) containing impurity carboxylic acids (A) at a concentration calculated as diglycolic acid (x) of 10.6 wt. % and nitrogen-containing substances (B) at a concentration calculated as ammonia (y) of 0.005 wt. % giving an effective concentration (x+100y) of depolymerization-obstructing substances of 11 wt. %.

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Abstract

Glycolide production through depolymerization of glycolic acid oligomer is stabilized by controlling impurities in the glycolic acid oligomer to allow economical and effective production of glycolide. More specifically, the depolymerization system is controlled to suppress an effective concentration (x+100y wt. %) of depolymerization-obstructing substances calculated as a total of a concentration calculated as diglycolic acid (of x wt. %) of hydroxyl group-free impurity carboxylic acids (A) and 100 times a concentration calculated as ammonia (of y wt. %) of nitrogen-containing substances (B), respectively with respect to the starting glycolic acid oligomer in the depolymerization system, to at most 15 wt. %.

Description

FIELD OF THE INVENTION[0001]The present invention relates a commercially useful process for producing glycolide which is a cyclic dimer ester of glycolic acid, and a glycolic acid oligomer used as a starting material in the process.RELATED BACKGROUND ART[0002]Glycolide is useful as a starting material for production of polyglycolic acid which is a resin material excellent in hydrolyzability in living things or in the earth and also excellent in gas-barrier property. More specifically, polyglycolic acid is a polymer having a recurring unit of —(—CH2—CO—O—)— obtained by dehydro-polycondensation of glycolic acid (i.e., α-hydroxyacetic acid), but according to this process, it is difficult to obtain polyglycolic acid of a high molecular weight. Accordingly, a process of ring-opening polymerization of glycolide (CH2—CO—O)2 which is a cyclic dimer ester of glycolic acid to obtain a high-molecular weight polyglycolic acid, is advantageous (Patent document 1 listed below).[0003]In order to p...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07D319/12C08F301/00
CPCC07D319/12
Inventor OGAWA, TOMOYUKIKAGOSHIMA, MASARU
Owner KUREHA KAGAKU KOGYO KK
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